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Vacation Rentals in Kailua, Oahu, Hawaii

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  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 88 Rentals in Kailua
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From
$5,500
Per Night
10 Bedrooms, 11 Bathrooms, Sleeps 18
37 photos Details
Reviews (4) Make Inquiry
From
$108
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details
Reviews (18) Make Inquiry
From
$300
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (15) Make Inquiry
Also consider
Beautiful Lanikai Home
3 Bedrooms, sleeps 8
$425 / night
Beautiful Fully Furnished 2 BR/2BA Kailua Home in Garden Setting
2 Bedrooms, sleeps 6
$225 / night
Nohea
4 Bedrooms, sleeps 12
$650 / night
Maluhia -
4 Bedrooms, sleeps 6
$1,500 / night
From
$160
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
28 photos Details
Reviews (3) Make Inquiry
From
$147
Per Night
Studio, 1 Bathroom, Sleeps 3
17 photos Details
Reviews (20) Make Inquiry
From
$550
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (4) Make Inquiry
From
$4,900
Per Week
6 Bedrooms, 3 Bathrooms, Sleeps 11
17 photos Details
Reviews (1) Make Inquiry
From
$1,050
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
31 photos Details
Reviews (3) Make Inquiry
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From
$1,250
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details
Reviews (4) Make Inquiry
From
$95
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (18) Make Inquiry
From
$330
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (5) Make Inquiry
From
$725
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
26 photos Details
Reviews (1) Make Inquiry
From
$150
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (8) Make Inquiry
From
$179
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
16 photos Details
Reviews (1) Make Inquiry
From
$650
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
19 photos Details
Reviews (3) Make Inquiry
From
$1,600
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 14
29 photos Details
Reviews (12) Make Inquiry
From
$145
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
32 photos Details
Reviews (9) Make Inquiry
From
$900
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
19 photos Details
Reviews (1) Make Inquiry
From
$1,100
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 15
24 photos Details
Reviews (3) Make Inquiry
From
$800
Per Night
8 Bedrooms, 4 Bathrooms, Sleeps 18
18 photos Details
Reviews (3) Make Inquiry
From
$249
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
13 photos Details
Reviews (1) Make Inquiry
From
$146
Per Night
Studio, 1 Bathroom, Sleeps 2
7 photos Details
Reviews (1) Make Inquiry
From
$175
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (4) Make Inquiry
From
$175
Per Night
Studio, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (34) Make Inquiry
From
$195
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details
Reviews (6) Make Inquiry
From
$126
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details
Reviews (5) Make Inquiry
From
$265
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
13 photos Details
Reviews (13) Make Inquiry
From
$220
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details
Reviews (4) Make Inquiry
From
$125
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
20 photos Details
Reviews (15) Make Inquiry
From
$695
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
26 photos Details
Reviews (21) Make Inquiry
From
$395
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
16 photos Details
Reviews (23) Make Inquiry
From
$285
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 20
26 photos Details
Reviews (12) Make Inquiry
From
$175
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
41 photos Details
Reviews (10) Make Inquiry
From
$100
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Reviews (28) Make Inquiry
From
$475
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details
Reviews (2) Make Inquiry
From
$395
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (7) Make Inquiry
From
$1,950
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 7
22 photos Details
Reviews (1) Make Inquiry
From
$1,325
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
29 photos Details
Reviews (1) Make Inquiry
From
$79
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
25 photos Details
Reviews (1) Make Inquiry
From
$255
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details
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Book Online(41)
Use filters to find the best results!

Suitability

  • Wheelchair access (8)
  • Elder access (29)
  • Suitable for children (36)
  • Pet friendly (2)
  • Smoking allowed (0)

Amenities

  • Internet (74)
  • Grill (67)
  • Other outdoor space (59)
  • Parking (52)
  • Washer/Dryer (52)
  • View all amenities
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Book Online(41)

Suitability

  • Wheelchair access (8)
  • Elder access (29)
  • Suitable for children (36)
  • Pet friendly (2)
  • Smoking allowed (0)

Amenities

  • Internet (74)
  • Grill (67)
  • Other outdoor space (59)
  • Parking (52)
  • Washer/Dryer (52)
  • View all amenities
Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.